Enantioselective Total Synthesis of Aspergillide C

Enantioselective Total Synthesis of Aspergillide C

The first enantioselective total synthesis of aspergillide C, a cytotoxic 14-membered macrolide isolated from the marine-derived fungus Aspergillus ostianus, has been accomplished from a commercially available chiral glycidol derivative by a 12-step sequence involving an expeditious preparation of a...

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Bibliographic Details
Published in:Organic letters Vol. 11; no. 3; pp. 761 - 764
Main Authors: Nagasawa, Tomohiro, Kuwahara, Shigefumi
Format: Journal Article
Language:English
Published: United States American Chemical Society 05-02-2009
Subjects:
Epoxy Compounds - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Propanols - chemistry
Stereoisomerism
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Summary:The first enantioselective total synthesis of aspergillide C, a cytotoxic 14-membered macrolide isolated from the marine-derived fungus Aspergillus ostianus, has been accomplished from a commercially available chiral glycidol derivative by a 12-step sequence involving an expeditious preparation of a cyclic acetal intermediate and a trans-selective Ferrier-type two-carbon homologation reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802803x